Played two games for the Tassie Devils VFL side towards the end of 2006 and kicked ten at full-forward in a club game the same year. Drafted by the Demons as a key position player, either forward or in the backline, he debuted with two games in 2007 but couldn't find a permanent spot in the team.

In 2008 he moved permanently into defence and had a breakout season despite the Demons playing a wooden-spoon year. After his excellent year he was expected to feature prominently again in 2009 but suffered a season ending injury in the first round and did not return again until Round 3, 2010. He quickly re-established in Melbourne's defence and played every remaining game of the season.

He had another consistent year in 2011, marred only by missing a month of football after injuring himself in the Round 8 loss to North Melbourne. In 2012 Garland enjoyed his first full season, playing every game, and had a brief stint playing in the forward line during the middle of the year - most notably when he kicked the winning goal in the shock Round 10 victory over Essendon. Soon after he moved back into defence where he finished the year.

Garland's 2013 was his best yet, in an under siege defence, he stood up on a weekly basis and was rewarded with second in the club's Best and Fairest. After four nearly injury free seasons he had a delayed start to 2014 after being forced to undergo pre-season ankle surgery. He returned to play 14 games for the season but was not the dominant defender he had been the previous season. His year ended prematurely after he suffered a knee injury in the second last match of the season.

In 2015 he was again largely unimpeded by injury, and played 20 games in defence for the improved Demons. At the end of the season he signed a contract extension to the end of the 2018 season.

After several years as a regular he fell out of favour in 2016, playing just six games. A knee injury in the 2017 pre-season ended his year. That year he was appointed to the coaching panel of the Melbourne AFLW team. Garland retired at the end of 2017, and was named the coach of the Casey Demons womens team. Early in the 2018 season he returned to Tasmania for personal reasons, rejoining North Hobart as a player.